When returning to work after a period of time off, did you find it difficult to get a job again?
I never had any trouble. In fact, I usually had multiple offers (and my only mistake was occasionally chosing the wrong offer, like blowing off MSFT in 1987 and AOL in 1996).
But I had at least three things going for me:
1) The job market for software weenies was very strong whenever I did this (1981, 1985, 1987, 1996, 1999, and finally in 2002 (a good time to exit, I think)).
2) I was pretty self-confident, and sometimes I think that's more important in landing a job than smarts, experience, etc.
3) I started a couple of companies, which gave me valuable experience, made my resume look pretty good, and perhaps most importantly, it meant that my resume never had any gaps since I always kept a company "alive" even if I wasn't very actively participating. Great for tax breaks too